Cefpirome

Chemical compound

Pharmaceutical compound

Cefpirome
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01DE02 (WHO )
Identifiers
IUPAC name 1-{[(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium
CAS Number	84957-29-9 ^checkY
PubChem CID	6917674
ChemSpider	23089536 ^☒N
UNII	S72Q2F09HY
KEGG	D07649 ^checkY
ChEMBL	ChEMBL2106076 ^☒N
CompTox Dashboard (EPA)	DTXSID2048244 Edit this at Wikidata
Chemical and physical data
Formula	C₂₂H₂₂N₆O₅S₂
Molar mass	514.58 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CON=C(c1csc(n1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[n+]4cccc5c4CCC5)C(=O)[O-]
InChI InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20+/m1/s1^☒N Key:DKOQGJHPHLTOJR-XECLGWKCSA-N^☒N
^☒NcheckY (what is this?) (verify)

Cefpirome is a fourth-generation cephalosporin. Trade names include Cefrom, Keiten, Broact, and Cefir. Cefpirome is considered highly active against Gram-negative bacteria, including Pseudomonas aeruginosa , and Gram-positive bacteria.^{[citation needed ]}

Spectrum of bacterial susceptibility and resistance

Bacteroides fragilis , enterococci, Pseudomonas spp. and staphylococci are resistant to cefpirome sulfate, and some Haemophilus spp. and pneumococci have developed resistance to it to varying degrees.^[1]

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) ^# Benzathine benzylpenicillin ^# Procaine benzylpenicillin ^# Phenoxymethylpenicillin (V) ^# Propicillin ^‡ Pheneticillin ^‡ Azidocillin ^‡ Clometocillin ^‡ Penamecillin ^‡
β-lactamase resistant (2nd generation)	Cloxacillin ^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin ^‡

Aminopenicillins (3rd generation)	Amoxicillin ^# Ampicillin ^# (Pivampicillin Hetacillin ^‡ Bacampicillin ^‡ Lenampicillin Metampicillin ^‡ Talampicillin ^‡) Epicillin ^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin ^‡ / Carindacillin ^‡ Temocillin ^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin ^‡ Mezlocillin ^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin ^‡

1st generation	Cefazolin ^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone ^‡ Cefazaflur ^‡ Cefradine ^‡ Cefroxadine ^‡ Ceftezole ^‡ Cefaloglycin ^‡ Cefacetrile ^‡ Cefalonium ^‡ Cefaloridine ^‡ Cefalotin Cefatrizine ^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole ^‡ Cefonicid ^‡ Ceforanide ^‡ Cefuzonam ^‡ Cephamycin (Cefoxitin Cefotetan Cefminox ^‡ Cefbuperazone ^‡ Cefmetazole ^‡) Carbacephem (Loracarbef ^‡)
3rd generation	Cefixime ^# Ceftriaxone ^# Cefotaxime ^# Antipseudomonal (Ceftazidime ^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam ^‡ Cefetamet ^‡ Cefodizime ^‡ Cefpimizole ^‡ Cefsulodin ^‡ Cefteram ^‡ Ceftiolene ^‡ Oxacephem (Flomoxef Latamoxef ^‡)
4th generation	Cefepime Cefozopran ^‡ Cefpirome Cefquinome ^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol ^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Combinations

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin ^§

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

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